Organic electroluminescent compound and organic electroluminescent device comprising the same

ABSTRACT

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the compound according to the present disclosure, it is possible to produce an organic electroluminescent device having improved driving voltage, power efficiency, and/or lifetime properties compared to the conventional organic electroluminescent devices.

TECHNICAL FIELD

The present disclosure relates to an organic electroluminescent compoundand an organic electroluminescent device comprising the same.

BACKGROUND ART

An electroluminescent device (EL device) is a self-light-emittingdisplay device which has advantages in that it provides a wider viewingangle, a greater contrast ratio, and a faster response time. The firstorganic EL device was developed by Eastman Kodak in 1987, by using smallaromatic diamine molecules and aluminum complexes as materials forforming a light-emitting layer (see Appl. Phys. Lett. 51, 913, 1987).

An organic electroluminescent device (OLED) changes electric energy intolight by applying electricity to an organic electroluminescent material,and commonly comprises an anode, a cathode, and an organic layer betweenthe two electrodes. The organic layer of the OLED may comprise a holeinjection layer, a hole transport layer, a hole auxiliary layer, alight-emitting auxiliary layer, an electron blocking layer, alight-emitting layer, an electron buffer layer, a hole blocking layer,an electron transport layer, an electron injection layer, etc., ifnecessary. The materials used in the organic layer can be classifiedinto a hole injection material, a hole transport material, a holeauxiliary material, a light-emitting auxiliary material, an electronblocking material, a light-emitting material (including a host materialand a dopant material), an electron buffer material, a hole blockingmaterial, an electron transport material, an electron injectionmaterial, etc., depending on their functions. In the OLED, holes fromthe anode and electrons from the cathode are injected into alight-emitting layer by the application of electric voltage, andexcitons having high energy are produced by the recombination of theholes and electrons. The organic light-emitting compound moves into anexcited state by the energy and emits light from the energy when theorganic light-emitting compound returns to the ground state from theexcited state.

The selection of the compound comprised in the hole transport layer,etc. has been recognized as a means for improving device properties suchas hole transport efficiency to the light-emitting layer, luminousefficiency, and lifetime. Recently, the development of the organicelectroluminescent device having high efficiency and long lifetime hasemerged as an urgent task. In particular, the development of highlyexcellent material over conventional light-emitting materials isurgently required, considering the level of EL properties required formedium- and large-sized OLED panels.

Meanwhile, International Patent Publication No. 2019/235725 discloses acompound in which an amino group is attached to a naphthocarbazolederivative. In addition, Korean Patent Application Laid-Open No.2012-0116881 discloses a compound in which two amino groups are attachedto a naphthofluorene derivative. However, the aforementioned referencesdo not specifically disclose that a compound in which one amino group isattached to naphthalene-fused fluoren can improve the performance of anorganic electroluminescent device.

DISCLOSURE OF INVENTION Technical Problem

The objective of the present disclosure is to provide an organicelectroluminescent compound effective for producing an organicelectroluminescent device having low driving voltage, high powerefficiency, and/or improved lifetime properties.

Solution to Problem

The present inventors have found that the above objective can beachieved by an organic electroluminescent compound represented by thefollowing formula 1.

In formula 1,

R′₁ and R′₂, each independently, represent a substituted orunsubstituted (C1-C30)alkyl, a substituted or unsubstituted(C6-C30)aryl, or a substituted or unsubstituted (3- to30-membered)heteroaryl; or R′₁ and R′₂ may be linked to each other toform a ring(s), in which R′₁ and R′₂ may be the same as or differentfrom each other;

R₁ to R₄, each independently, represent hydrogen, deuterium, a halogen,a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted orunsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to30-membered)heteroaryl, a substituted or unsubstituted(C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, asubstituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted orunsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted orunsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted orunsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fusedring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromaticring(s), or -L₁-N—(Ar₁)(Ar₂); or may be linked to an adjacentsubstituent to form a ring(s);

with the proviso that any one of R₁'s to R₄'s represents-L₁-N—(Ar₁)(Ar₂);

L₁ represents a single bond, a substituted or unsubstituted(C6-C30)arylene, or a substituted or unsubstituted (3- to30-membered)heteroarylene:

Ar₁ and Ar₂, each independently, represent a substituted orunsubstituted (C1-C30)alkyl, a substituted or unsubstituted(C2-C30)alkenyl, a substituted or unsubstituted fused ring group of a(C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), asubstituted or unsubstituted (C6-C30)aryl, or a substituted orunsubstituted (3- to 30-membered)heteroaryl; and

m and p, each independently, represent an integer of 4; n and o, eachindependently, represent an integer of 2; and each of R₁ to each of R₄may be the same or different.

Advantageous Effects of Invention

The organic electroluminescent compound according to the presentdisclosure is possible to provide an organic electroluminescent devicehaving low driving voltage, high power efficiency, and/or improvedlifetime properties.

MODE FOR THE INVENTION

Hereinafter, the present disclosure will be described in detail.However, the following description is intended to explain thedisclosure, and is not meant in any way to restrict the scope of thedisclosure.

The term “an organic electroluminescent compound” in the presentdisclosure means a compound that may be used in an organicelectroluminescent device. If necessary, the organic electroluminescentcompound may be comprised in any layers constituting an organicelectroluminescent device.

The term “an organic electroluminescent material” in the presentdisclosure means a material that may be used in an organicelectroluminescent device, and may comprise at least one compound. Ifnecessary, the organic electroluminescent material may be comprised inany layers constituting an organic electroluminescent device. Forexample, the organic electroluminescent material may be a hole injectionmaterial, a hole transport material, a hole auxiliary material, alight-emitting auxiliary material, an electron blocking material, alight-emitting material (including a host material and a dopantmaterial), an electron buffer material, a hole blocking material, anelectron transport material, an electron injection material, etc.

Herein, the term “(C1-C30)alkyl” is meant to be a linear or branchedalkyl having 1 to 30 carbon atoms constituting the chain, in which thenumber of carbon atoms is preferably 1 to 10, and more preferably 1 to6. The above alkyl may include methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term“(C3-C30)cycloalkyl” is meant to be a mono- or polycyclic hydrocarbonhaving 3 to 30 ring backbone carbon atoms, in which the number of carbonatoms is preferably 3 to 20, and more preferably 3 to 7. The abovecycloalkyl may include cyclopropyl, cyclobutyl, cydopentyl, cyclohexyl,cydopentylmethyl, cyclohexylmethyl, etc. The term “(3- to7-membered)heterocycloalkyl” is meant to be a cycloalkyl having 3 to 7ring backbone atoms, and including at least one heteroatom selected fromthe group consisting of B, N, O, S, Si, P, Te, and Se, and preferablythe group consisting of O, S, N, Te, and Se. The above heterocydoalkylmay include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.The term “(C6-C30)aryl” or “(C6-C30)arylene” is meant to be a monocyclicor fused ring radical derived from an aromatic hydrocarbon having 6 to30 ring backbone carbon atoms. The above aryl(ene) may be partiallysaturated, and may comprise a spiro structure. The above aryl mayinclude phenyl, biphenyl, terphenyl, naphthyl, binaphthyl,phenyinaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl,diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl,phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl,triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl,fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluoren]yl,spiro[cyclopenten-fluoren]yl, spiro[dihydroinden-fluoren]yl, azulenyl,tetramethyldihydrophenanthrenyl, etc. Specifically, the aryl may includephenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl,benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl,9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl,3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl,benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl,4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl,9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl,dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl,m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl,p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl,4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl,o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl,o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl,p-(2-phenylpropyl)phenyl, 4′-methylbiphenyl,4″-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl,9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl,9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl,9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl,9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl,11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl,11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl,11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl,11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl,11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl,11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl,11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl,11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl,11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl,11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl,11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl,11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl,11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl,11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl,11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl,11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl,11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl,11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl,11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl,11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl,11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl,11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl,11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl,11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl,11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl,11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl,11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl,11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl,11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl,11,11-diphenyl-10-benzo[c]fluorenyl,9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl,9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl,9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl,9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, etc.

The term “(3- to 30-membered)heteroaryl” or “(3- to30-membered)heteroarylene” in the present disclosure is meant to be anaryl(ene) having 3 to 30 ring backbone atoms and including at least oneheteroatom(s) selected from the group consisting of B, N, O, S, Si, P,Te, and Se. The number of heteroatoms is preferably 1 to 4. The aboveheteroaryl(ene) may be a monocyclic ring or a fused ring condensed withat least one benzene ring; may be partially saturated; may be one formedby linking at least one heteroaryl or aryl group to a heteroaryl(ene)group via a single bond(s); and may comprise a spiro structure. Theabove heteroaryl may include a monocyclic ring-type heteroaryl such asfuryl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl,thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl,triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl,pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-typeheteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl,dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl,naphthobenzofuranyl, naphthobenzothiophenyl, benzofuroquinolyl,benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl,naphthofuropyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl,naphthyridinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl,naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl,benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl,naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl,benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl,benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl,quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl,quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl,dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl,dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridyl,chromenoquinazolinyl, thiochromenoquinazolinyl,dimethylbenzoperimidinyl, indolocarbazolyl, indenocarbazolyl, etc. Morespecifically, the heteroaryl may include 1-pyrrolyl, 2-pyrrolyl,3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl,1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl,1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl,6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridyl,3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl,8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl,4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl,3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl,2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl,5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl,3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl,6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl,4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl,1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl,6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl,5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl,3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl,azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl,azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl,azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl,2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl,6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl,9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl,3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl,5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl,3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl,2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl,3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl,2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl,2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl,4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl,2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl,2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl,1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl,4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl,2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl,4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl,6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl,8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl,10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl,2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl,4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl,6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl,8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl,10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl,2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl,4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl,6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl,8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl,10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl,2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl,4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl,6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl,8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl,10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl,2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl,4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl,1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl,3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl,5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl,7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl,9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl,2-benzofuro[3,2-d]pyrmidinyl, 6-benzofuro[3,2-d]pyrmidinyl,7-benzofuro[3,2-d]pyrmidinyl, 8-benzofuro[3,2-d]pyrmidinyl,9-benzofuro[3,2-d]pyrmidinyl, 2-benzothio[3,2-d]pyrimidinyl,6-benzothio[3,2-d]pyrmidinyl, 7-benzothio[3,2-d]pyrimidinyl,8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrmidinyl,2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl,7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl,9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl,6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl,8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl,1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl,1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl,1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl,4-dibenzoselenophenyl, etc. In the present disclosure, the term“halogen” includes F, Cl, Br, and I.

In addition, “ortho (o-),” “meta (m-),” and “para (p-)” are prefixes,which represent the relative positions of substituents respectively.Ortho indicates that two substituents are adjacent to each other, andfor example, when two substituents in a benzene derivative occupypositions 1 and 2, it is called an ortho position. Meta indicates thattwo substituents are at positions 1 and 3, and for example, when twosubstituents in a benzene derivative occupy positions 1 and 3, it iscalled a meta position. Para indicates that two substituents are atpositions 1 and 4, and for example, when two substituents in a benzenederivative occupy positions 1 and 4, it is called a para position.

Herein, “substituted” in the expression “substituted or unsubstituted”means that a hydrogen atom in a certain functional group is replacedwith another atom or another functional group, i.e., a substituent, andalso includes that the hydrogen atom is replaced with a group formed bya linkage of two or more substituents of the above substituents. Forexample, the “group formed by a linkage of two or more substituents” maybe pyridine-triazine. That is, pyridine-triazine may be interpreted as aheteroaryl substituent, or as substituents in which two heteroarylsubstituents are linked. Herein, the substituent(s) of the substitutedalkyl, the substituted alkenyl, the substituted alkynyl, the substitutedaryl, the substituted arylene, the substituted heteroaryl, thesubstituted heteroarylene, the substituted cycloalkyl, the substitutedalkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl,the substituted alkyldiarylsilyl, the substituted triarylsilyl, thesubstituted fused ring group of an aliphatic ring(s) and an aromaticring(s), the substituted alkylarylamino, the substituted mono- ordi-alkylamino, the substituted mono- or di-arylamino, the substitutedmono- or di-heteroarylamino, and the substituted arylheteroarylamino,each independently, are at least one selected from the group consistingof deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; aphosphineoxide; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenylunsubstituted or substituted with a (C6-C30)aryl(s); a (C2-C30)alkynyl;a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a(C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a(C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroarylunsubstituted or substituted with at least one of deuterium and a(C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with atleast one of deuterium, a halogen(s), a cyano(s), a (C1-C30)alkyl(s), a(C6-C30)aryl(s), (3- to 30-membered)heteroaryl(s), atri(C6-C30)arylsilyl(s), and a tri(C6-C30)arylgermanyl(s); atri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; adi(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; atri(C1-C30)alkylgermanyl; a tri(C6-C30)arylgermanyl; adi(C1-C30)alkyl(C6-C30)arylgermanyl; a(C1-C30)alkyldi(C6-C30)arylgermanyl; a fused ring group of a (C3-C30)aliphatic ring(s) and a (C6-C30) aromatic ring(s); an amino; a mono- ordi-(C1-C30)alkylamino; a mono- or di-(C2-C30)alkenylamino; a mono- ordi-(C6-C30)arylamino unsubstituted or substituted with a(C1-C30)alkyl(s); a mono- or di-(3- to 30-membered)heteroarylamino; a(C1-C30)alkyl(C2-C30)alkenylamino; a (C1-C30)alkyl(C6-C30)arylamino; a(C1-C30)alkyl(3- to 30-membered)heteroarylamino; a(C2-C30)alkenyl(C6-C30)arylamino; a (C2-C30)alkenyl(3- to30-membered)heteroarylamino; a (C6-C30)aryl(3- to30-membered)heteroarylamino; a (C1-C30)alkylcarbonyl; a(C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a(C6-C30)arylphosphinyl; a di(C6-C30)arylboronyl; adi(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a(C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl, or thecombination thereof. According to one embodiment of the presentdisclosure, the substituent(s), each independently, are at least oneselected from the group consisting of deuterium; a halogen; a cyano; a(C1-C20)alkyl; a (C2-C20)alkenyl unsubstituted or substituted with a(C6-C25)aryl(s); a (C6-C25)aryl unsubstituted or substituted with atleast one of deuterium, a halogen(s), a cyano(s), a (C1-C20)alkyl(s), a(C6-C25)aryl(s), a (5- to 20-membered)heteroaryl(s), atri(C6-C18)arylsilyl(s), and a tri(C6-C18)arylgermanyl(s); a (5- to25-membered)heteroaryl unsubstituted or substituted with at least one ofdeuterium and a (C6-C25)aryl(s); a tri(C6-C18)arylsilyl; atri(C6-C18)arylgermanyl; and a (C6-C25)aryl(C1-C20)alkyl. According toanother embodiment of the present disclosure, the substituent(s), eachindependently, are at least one selected from the group consisting ofdeuterium; a cyano; a (C1-C10)alkyl; a (C2-C10)alkenyl unsubstituted orsubstituted with a (C6-C18)aryl(s); a (C6-C25)aryl unsubstituted orsubstituted with at least one of deuterium, a halogen(s), a cyano(s), a(C1-C10)alkyl(s), a (C6-C18)aryl(s), (5- to 20-membered)heteroaryl(s), atri(C6-C18)arylsilyl(s), and a tri(C6-C18)arylgermanyl(s); a (5- to20-membered)heteroaryl unsubstituted or substituted with at least one ofdeuterium and a (C6-C18)aryl(s); a tri(C6-C18)arylsilyl; atri(C6-C18)arylgermanyl; and a (C6-C18)aryl(C1-C10)alkyl. For example,the substituent(s), each independently, may be any one selected from thegroup consisting of deuterium, a cyano, a methyl, a tert-butyl, aethylene substituted with a phenyl(s), a substituted or unsubstitutedphenyl, a substituted or unsubstituted naphthyl, a biphenyl; aphenanthrenyl, a terphenyl, a chrysenyl, a benzo[c]phenanthryl, atriphenylenyl, a dimethylfluorenyl, a diphenylfluorenyl, adimethylbenzofluorenyl, a spirobifluorenyl, a pyridyl, a pyrimidinyl, atriazinyl substituted with a phenyl(s), an indolyl, a dibenzofuranylunsubstituted or substituted with at least one of deuterium and aphenyl(s), a dibenzothiophenyl, a carbazolyl unsubstituted orsubstituted with at least one of a phenyl(s) and a biphenyl(s), aphenylpropyl, a dibenzotelluriumyl, a dibenzoselenophenyl, abenzonaphthofuranyl, a benzonaphthothiophenyl, a phenanthrooxazolylsubstituted with a phenyl(s), a triphenylsilyl, and a triphenylgermanyl,or the combination thereof. The substituent(s) of the substituted phenylmay be at least one selected from the group consisting of deuterium, acyano, a fluoro, a methyl, a naphthyl, a carbazolyl, a triphenylsilyl, atriphenylgermanyl, and a dibenzotellurumyl. The substituent(s) of thesubstituted naphthyl may be at least one selected from the groupconsisting of a phenyl, a biphenyl, and a chrysenyl.

Herein, a ring formed by a linkage of adjacent substituents means thatat least two adjacent substituents are linked to or fused with eachother to form a substituted or unsubstituted, mono- or polycyclic, (3-to 30-membered) alicyclic or aromatic ring, or the combination thereof.Preferably, the ring may be a substituted or unsubstituted, mono- orpolycyclic, (3- to 26-membered) alicyclic or aromatic ring, or thecombination thereof. More preferably, the ring may be a mono- orpolycyclic, (5- to 25-membered) aromatic ring unsubstituted orsubstituted with at least one of a (C1-C6)alkyl(s), a (C6-C18)aryl(s)and a (3- to 20-membered)heteroaryl(s). In addition, the formed ring maycontain at least one heteroatom selected from B, N, O, S, Si, P, Te, andSe, and preferably at least one heteroatom selected from N, O, S, Te,and Se. For example, the ring may be a benzene ring, a cyclopentanering, an indene ring, an indane ring, a fluorene ring, a phenanthrenering, an indole ring, a benzofuran ring unsubstituted or substitutedwith a phenyl(s), a benzothiophene ring unsubstituted or substitutedwith a phenyl(s), a xanthene ring, etc. The ring may also form a spiroring(s).

Herein, heteroaryl, heteroarylene, and heterocycloalkyl, eachindependently, may contain at least one heteroatom selected from thegroup consisting of B, N, O, S, Si, P, Te, and Se. In addition, theheteroatom may be bonded to at least one selected from the groupconsisting of hydrogen, deuterium, a halogen, a cyano, a substituted orunsubstituted (C1-C30)alkyl, a substituted or unsubstituted(C6-C30)aryl, a substituted or unsubstituted (3- to30-membered)heteroaryl, a substituted or unsubstituted(C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, asubstituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted orunsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted orunsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted orunsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono-or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- ordi-(C2-C30)alkenylamino, a substituted or unsubstituted mono- ordi-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to30-membered)heteroarylamino, a substituted or unsubstituted(C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted(C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted(C1-C30)alkyl(3- to 30-membered)heteroarylamino, a substituted orunsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted orunsubstituted (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, and asubstituted or unsubstituted (C6-C30)aryl(3- to30-membered)heteroarylamino.

In formula 1, R′₁ and R′₂, each independently, represent a substitutedor unsubstituted (C1-C30)alkyl, a substituted or unsubstituted(C6-C30)aryl, or a substituted or unsubstituted (3- to30-membered)heteroaryl; or R′₁ and R′₂ may be linked to each other toform a ring(s). R′₁ and R′₂ may be the same as or different from eachother. According to one embodiment of the present disclosure, R′₁ andR′₂, each independently, represent a substituted or unsubstituted(C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or asubstituted or unsubstituted (5- to 25-membered)heteroaryl; or R′₁ andR′₂ may be linked to each other to form a ring(s). According to anotherembodiment of the present disclosure, R′₁ and R′₂, each independently,represent an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl,or an unsubstituted (5- to 20-membered)heteroaryl; or R′₁ and R′₂ may belinked to each other to form a spiro ring. For example, R′₁ and R′₂,each independently, represent a methyl, an ethyl, a propyl, a phenyl, anaphthyl, a pyridyl, etc.; or R′₁ and R′₂ may be linked to each other toform a spirofluorene ring or a spiroindane ring, etc.

In formula 1, m and p, each independently, represent an integer of 4; nand o, each independently, represent an integer of 2; and each of R₁ toeach of R₄ may be the same or different.

In formula 1, R₁ to R₄, each independently, represent hydrogen,deuterium, a halogen, a cyano, a substituted or unsubstituted(C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, asubstituted or unsubstituted (3- to 30-membered)heteroaryl, asubstituted or unsubstituted (C3-C30)cycloalkyl, a substituted orunsubstituted (C1-C30)alkoxy, a substituted or unsubstitutedtri(C1-C30)alkylsilyl, a substituted or unsubstituteddi(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstitutedtri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring group ofa (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), or-L₁-N—(Ar₁)(Ar₂); or may be linked to an adjacent substituent to form aring(s); with the proviso that any one of R₁'s to R₄'s represents-L₁-N—(Ar₁)(Ar₂). According to one embodiment of the present disclosure,R₁ to R₄, each independently, represent hydrogen, or -L₁-N—(Ar₁)(Ar₂).

L₁ represents a single bond, a substituted or unsubstituted(C6-C30)arylene, or a substituted or unsubstituted (3- to30-membered)heteroarylene. According to one embodiment of the presentdisclosure, L₁ represents a single bond, a substituted or unsubstituted(C6-C25)arylene, or a substituted or unsubstituted (5- to25-membered)heteroarylene. According to another embodiment of thepresent disclosure, L₁ represents a single bond, a (C6-C18)aryleneunsubstituted or substituted with a (C6-C18)aryl(s), or an unsubstituted(5- to 20-membered)heteroarylene. For example, L₁ may be a single bond,a phenylene unsubstituted or substituted with a phenyl(s), anaphthylene, a biphenylene, a dibenzothiophenylene, a dibenzofuranylene,etc.

Ar₁ and Ar₂, each independently, represent a substituted orunsubstituted (C1-C30)alkyl, a substituted or unsubstituted(C2-C30)alkenyl, a substituted or unsubstituted fused ring group of a(C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), asubstituted or unsubstituted (C6-C30)aryl, or a substituted orunsubstituted (3- to 30-membered)heteroaryl. Ar₁ and Ar₂ may be the sameor different. According to one embodiment of the present disclosure, Ar₁and Ar₂, each independently, represent a substituted or unsubstituted(C6-C25)aryl, or a substituted or unsubstituted (5- to25-membered)heteroaryl. According to another embodiment of the presentdisclosure, Ar₁ and Ar₂, each independently, represent a substituted orunsubstituted (C6-C24)aryl, or a (5- to 20-membered)heteroarylunsubstituted or substituted with a (C6-C18)aryl(s). The substituent(s)of the substituted aryl may be any one selected from the groupconsisting of a (C1-C10)alkyl, a (C2-C10)alkenyl, a (C6-C18)aryl, a (5-to 15-membered)heteroaryl, and a (C6-C18)aryl(C1-C10)alkyl; or thecombination thereof. For example, Ar₁ and Ar₂, each independently, maybe a substituted or unsubstituted phenyl, a naphthyl, a phenylnaphthyl,a naphthylphenyl, a biphenyl, a phenanthrenyl, a terphenyl, aquaterphenyl, a triphenylenyl, a chrysenyl, a dimethylfluorenyl, adiphenylfluorenyl, a benzofuranyl, a benzothiophenyl, a dibenzofuranylunsubstituted or substituted with a phenyl(s), a dibenzothiophenylunsubstituted or substituted with a phenyl(s), a dibenzoselenophenylunsubstituted or substituted with a phenyl(s), a phenylcarbazolyl, aphenoxazinyl substituted with a phenyl(s), etc. The substituent(s) ofthe phenyl may be at least one selected from the group consisting of amethyl, a tert-butyl, a triphenylethylenyl, a dimethylfluorenyl, adibenzofuranyl, a dibenzothiophenyl, an indolyl, a pyridyl, apyrimidinyl, a carbazolyl, and a phenylpropyl, etc.

The formula 1 may be represented by the following formula 1-1.

In formula 1-1, R′₁, R′₂, R₁ to R₄, and m to p are as defined in formula1 above.

The formula 1 may be represented by any one of the following formulas1-1-1 to 1-1-4.

In formulas 1-1-1 to 1-1-4, R′₁, R′₂, L₁, Ar₁, Ar₂, and m to p are asdefined in formula 1 above.

In formulas 1-1-1 to 1-14, m′ and p′, each independently, represent aninteger of 3; and n′ and o′, each independently, represent an integer of1.

In formulas 1-1-1 to 1-14, R₁ to R₄, each independently, representhydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted(C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, asubstituted or unsubstituted (3- to 30-membered)heteroaryl, asubstituted or unsubstituted (C3-C30)cycloalkyl, a substituted orunsubstituted (C1-C30)alkoxy, a substituted or unsubstitutedtri(C1-C30)alkylsilyl, a substituted or unsubstituteddi(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstitutedtri(C6-C30)arylsilyl, or a substituted or unsubstituted fused ring groupof a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s); or maybe linked to an adjacent substituent to form a ring(s). For example, R₁to R₄ may be hydrogen.

The formula 1 may be represented by any one of the following formulas1-1-1-1 to 1-1-1-12.

In formulas 1-1-1-1 to 1-1-1-12, R′₁, R′₂, L₁, Ar₁, Ar₂, and m to p areas defined in formula 1 above.

In formulas 1-1-1-1 to 1-1-1-12, m′ and p′, each independently,represent an integer of 3; and n′ and o′, each independently, representan integer of 1.

In formulas 1-1-1-1 to 1-1-1-12, R₁ to R₄, each independently, representhydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted(C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, asubstituted or unsubstituted (3- to 30-membered)heteroaryl, asubstituted or unsubstituted (C3-C30)cycloalkyl, a substituted orunsubstituted (C1-C30)alkoxy, a substituted or unsubstitutedtri(C1-C30)alkylsilyl, a substituted or unsubstituteddi(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstitutedtri(C6-C30)arylsilyl, or a substituted or unsubstituted fused ring groupof a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s); or maybe linked to an adjacent substituent to form a ring(s). For example, R₁to R₄ may be hydrogen.

The compound represented by formula 1 may be at least one selected fromthe group consisting of the following compounds, but is not limitedthereto.

The organic electroluminescent compound of the present disclosure may beproduced by a synthetic method known to one skilled in the art, and forexample, by referring to the following reaction schemes 1 to 4, but isnot limited thereto.

In reaction schemes 1 to 4, R′₁, R′₂, L₁, Ar₁, and Ar₂ are as defined informula 1.

Although illustrative synthesis examples of the compound represented byformula 1 are described above, one skilled in the art will be able toreadily understand that all of them are based on a Buchwald-Hartwigcross-coupling reaction, an N-arylation reaction, a H-mont-mediatedetherification reaction, a Miyaura borylation reaction, a Suzukicross-coupling reaction, an Intramolecular acid-induced cyclizationreaction, a Pd(II)-catalyzed oxidative cyclization reaction, a Grignardreaction, a Heck reaction, a Cyclic Dehydration reaction, an SN₁substitution reaction, an SN₂ substitution reaction, and aPhosphine-mediated reductive cyclization reaction, etc., and thereactions above proceed even when substituents which are defined informula 1 above, but are not specified in the specific synthesisexamples, are bonded.

A host compound, which can be used in combination with the compound ofthe present disclosure, includes a compound represented by any one ofthe following formulas 11 to 15, but is not limited thereto.

In formulas 11 to 15,

Ma represents a substituted or unsubstituted (C6-C30)aryl, a substitutedor unsubstituted mono- or di-(C6-C30)arylamino, a substituted orunsubstituted mono- or di-(3- to 30-membered)heteroarylamino, asubstituted or unsubstituted (C6-C30)aryl(3- to30-membered)heteroarylamino, or a substituted or unsubstituted (3- to30-membered)heteroaryl;

La represents a single bond, a substituted or unsubstituted(C6-C30)arylene, or a substituted or unsubstituted (3- to30-membered)heteroarylene;

A represents S, O, N(Re), C(Rf)(Rg), Te, or Se;

ring B represents a naphthalene ring or a phenanthrene ring;

Ra to Rd, and Rh to Rk, each independently, represent hydrogen,deuterium, a halogen, a cyano, a substituted or unsubstituted(C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, asubstituted or unsubstituted (C2-C30)alkynyl, a substituted orunsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted(C6-C30)aryl, a substituted or unsubstituted (3- to30-membered)heteroaryl, a substituted or unsubstitutedtri(C1-C30)alkylsilyl, a substituted or unsubstitutedtri(C6-C30)arylsilyl, a substituted or unsubstituteddi(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted(C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono-or di-(C1-C30)alkylamino, a substituted or unsubstituted(C1-C30)alkyl(C6-C30)arylamino, or a substituted or unsubstituted mono-or di-(C6-C30)arylamino; or may be linked to an adjacent substituent toform a ring(s);

Re to Rg, each independently, represent hydrogen, deuterium, a halogen,a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted orunsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to30-membered)heteroaryl, a substituted or unsubstituted(C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, asubstituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted orunsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted orunsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted orunsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono-or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- ordi-(C6-C30)arylamino, or a substituted or unsubstituted(C1-C30)alkyl(C6-C30)arylamino; and Rf and Rg may be linked to eachother to form a ring(s);

w to y, q, and r, each independently, represent an integer of 1 to 4; zrepresents an integer of 1 to 3; and a and t, each independently,represent an integer of 1 or 2; n represents an integer of 1 to 9; andeach of Ra to each of Rd, each of Ri to each of Rk, and each of La maybe the same or different; and

the heteroaryl(ene) comprises at least one heteroatom selected from thegroup consisting of B, N, O, S, Si, P, Te, and Se.

According to one embodiment, Ma represents a substituted orunsubstituted phenyl, a substituted or unsubstituted pyridyl, asubstituted or unsubstituted pyrimidinyl, a substituted or unsubstitutedtriazinyl, a substituted or unsubstituted quinazolinyl, a substituted orunsubstituted quinoxalinyl, a substituted or unsubstitutedbenzoquinazolinyl, a substituted or unsubstituted benzoquinoxalinyl, asubstituted or unsubstituted dibenzofuranyl, a substituted orunsubstituted dibenzothiophenyl, a substituted or unsubstituteddibenzotellurumyl, a substituted or unsubstitutedbenzofuranopyrimidinyl, a substituted or unsubstitutedbenzothienopyrimidinyl, a substituted or unsubstituted benzoxazolyl,etc.; and the substituent(s) thereof, each independently, may be any oneselected from the group consisting of a substituted or unsubstitutedphenyl, a substituted or unsubstituted naphthyl, a biphenyl, aphenanthrenyl, a terphenyl, a chrysenyl, a benzo[c]phenanthryl, atriphenylenyl, a dimethylfluorenyl, a diphenylfluorenyl, adimethylbenzofluorenyl, a spirobifluorenyl, a pyridyl, a pyrimidinyl, atriazinyl substituted with a phenyl(s), a dibenzofuranyl unsubstitutedor substituted with deuterium and/or a phenyl(s), a dibenzothiophenyl, acarbazolyl unsubstituted or substituted with a phenyl(s) and/or abiphenyl(s), a dibenzotelluriumyl, a dibenzoselenophenyl, abenzonaphthofuranyl, a benzonaphthothiophenyl, a phenanthrooxazolylsubstituted with a phenyl(s), a triphenylsilyl, and a triphenylgermanyl;or the combination thereof. The substituent(s) of the substituted phenylmay be at least one selected from the group consisting of deuterium, acyano, a fluoro, a methyl, a naphthyl, a carbazolyl, a triphenylsilyl, atriphenylgermanyl, and a dibenzotelluriumyl. The substituent(s) of thesubstituted naphthyl may be at least one selected from the groupconsisting of a phenyl, a biphenyl, and a chrysenyl.

According to one embodiment, La represents a single bond; a(C6-C25)arylene unsubstituted or substituted with at least one selectedfrom the group consisting of deuterium, a (C1-C30)alkyl, and a(C6-C30)aryl; or a (5- to 25-membered)heteroarylene unsubstituted orsubstituted with a (C6-C30)aryl(s). For example, La may be a singlebond; a phenylene unsubstituted or substituted with at least one ofdeuterium and a phenyl(s); a naphthylene unsubstituted or substitutedwith deuterium; a biphenylene unsubstituted or substituted with aphenyl(s); a phenanthrenylene; a terphenylene; a dimethylfluorenylene; apyridylene; a dibenzofuranylene; a dibenzothiophenylene; aphenylcarbazolylene; a quinoxalinylene substituted with a phenyl(s); ora quinazolinylene, etc.

According to one embodiment, Ra to Rd, and Rh to Rk, each independently,represent hydrogen, deuterium, a cyano, a substituted or unsubstituted(C1-C20)alkyl, a substituted or unsubstituted (C6-C30)aryl, or asubstituted or unsubstituted (5- to 20-membered)heteroaryl; or may belinked to an adjacent substituent to form a substituted orunsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic oraromatic ring, or the combination thereof. For example, Ra to Rd, and Rito Rk, each independently, may be hydrogen, deuterium, a cyano, amethyl, a phenyl, a naphthyl, a biphenyl unsubstituted or substitutedwith deuterium, a phenylnaphthyl, a naphthylphenyl, a phenanthrenyl, adimethylfluorenyl, a dibenzofuranyl unsubstituted or substituted with aphenyl(s), a dibenzothiophenyl unsubstituted or substituted with aphenyl(s), or a carbazolyl unsubstituted or substituted with aphenyl(s), etc.; or may be linked to an adjacent substituent to form abenzene ring, a benzofuran ring unsubstituted or substituted with aphenyl(s), or a benzothiophene ring unsubstituted or substituted with aphenyl(s), etc. For example, Rh may be a substituted phenyl, a naphthylunsubstituted or substituted with a diphenyltriazinyl(s), a biphenyl, aphenanthrenyl, a dimethylfluorenyl, a pyridyl unsubstituted orsubstituted with a phenyl(s), a dibenzothiophenyl, a dibenzofuranyl, aphenylcarbazolyl, etc. The substituent(s) of the substituted phenyl maybe at least one selected from the group consisting of deuterium, acyano, a triazinyl substituted with a phenyl(s), a triphenylsilyl, and atriphenylgermanyl.

According to one embodiment, Re to Rg, each independently, represent anunsubstituted (C1-C20)alkyl, an unsubstituted (C6-C25)aryl, or anunsubstituted (5- to 20-membered)heteroaryl; and Rf and Rg may be linkedto each other to form a substituted or unsubstituted, mono- orpolycyclic, (3- to 30-membered) alicyclic or aromatic ring, or thecombination thereof. For example, Re may be a phenyl or adibenzotelluriumyl. For example, Rf and Rg, each independently, may be amethyl or a phenyl, etc.; or Rf and Rg may be linked to each other toform a spirofluorene ring.

The compound represented by formula 11 may be at least one selected fromthe group consisting of the following compounds, but is not limitedthereto.

The compound represented by formula 12 may be at least one selected fromthe group consisting of the following compounds, but is not limitedthereto.

The compound represented by formula 13 or 14 may be at least oneselected from the group consisting of the following compounds, but isnot limited thereto.

The compound represented by formula 15 may be at least one selected fromthe group consisting of the following compounds, but is not limitedthereto.

The dopant comprised in the organic electroluminescent device of thepresent disclosure may be at least one phosphorescent or fluorescentdopant, and is preferably a phosphorescent dopant. The phosphorescentdopant material applied to the organic electroluminescent device of thepresent disclosure is not particularly limited, but may be preferablyselected from the group consisting of the metallated complex compoundsof iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), morepreferably selected from the group consisting of ortho-metallatedcomplex compounds of iridium (Ir), osmium (Os), copper (Cu), andplatinum (Pt), and even more preferably ortho-metallated iridium complexcompounds.

The dopant comprised in the organic electroluminescent device of thepresent disclosure may be a compound represented by the followingformula 101, but is not limited thereto.

L is any one selected from the following structures 1 to 3:

R₁₀₀ to R₁₀₃, each independently, represent hydrogen, deuterium, ahalogen, a (C1-C30)alkyl unsubstituted or substituted with deuteriumand/or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl,a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted orunsubstituted (3- to 30-membered)heteroaryl, or a substituted orunsubstituted (C1-C30)alkoxy; or may be linked to an adjacentsubstituent to form a ring(s), e.g., a substituted or unsubstituted,quinoline, benzofuropyridine, benzothienopyridine, indenopyridine,benzofuroquinoline, benzothienoquinoline, or indenoquinoline ring,together with pyridine;

R₁₀₄ to R₁₀₇, each independently, represent hydrogen, deuterium, ahalogen, a (C1-C30)alkyl unsubstituted or substituted with deuteriumand/or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl,a substituted or unsubstituted (C6-C30)aryl, a substituted orunsubstituted (3- to 30-membered)heteroaryl, a cyano, or a substitutedor unsubstituted (C1-C30)alkoxy; or may be linked to an adjacentsubstituent to form a ring(s), e.g., a substituted or unsubstituted,naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine,benzofuropyridine, or benzothienopyridine ring, together with benzene;

R₂₀₁ to R₂₂₀, each independently, represent hydrogen, deuterium, ahalogen, a (C1-C30)alkyl unsubstituted or substituted with deuteriumand/or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl,or a substituted or unsubstituted (C6-C30)aryl; or may be linked to anadjacent substituent to form a substituted or unsubstituted ring(s); and

s represents an integer of 1 to 3.

The specific examples of the dopant compound are as follows, but are notlimited thereto.

The compound represented by formula 1 of the present disclosure may becomprised in one or more layers constituting the organicelectroluminescent device, for example, at least one layer selected fromthe group consisting of a hole injection layer, a hole transport layer,a hole auxiliary layer, a light-emitting auxiliary layer, alight-emitting layer, an electron transport layer, an electron bufferlayer, an electron injection layer, an interlayer, a hole blockinglayer, and an electron blocking layer. Each of the layers may be furtherconfigured as a plurality of layers.

In addition, the compound represented by formula 1 of the presentdisclosure may be comprised in the hole transport zone and/or thelight-emitting layer, but is not limited thereto. The compoundrepresented by formula 1 of the present disclosure may be comprised inthe hole transport zone as at least one of a hole injection material, ahole transport material, a hole auxiliary material, a light-emittingauxiliary layer material, and an electron blocking material, e.g., as ahole transport material. Furthermore, the compound represented byformula 1 of the present disclosure may be comprised in thelight-emitting layer as a host, and may be used as a host having holetransport properties among hosts.

The present disclosure may comprise a hole transport zone between ananode and a light-emitting layer, and the hole transport zone maycomprise at least one of a hole injection layer, a hole transport layer,a hole auxiliary layer, a light-emitting auxiliary layer and an electronblocking layer. The hole injection layer, the hole transport layer, thehole auxiliary layer, the light-emitting auxiliary layer and theelectron blocking layer, respectively, may be a single layer or aplurality of layers in which two or more layers are stacked. The holeinjection layer may be multi-layers in order to lower the hole injectionbarrier (or hole injection voltage) from the anode to the hole transportlayer or the electron blocking layer, wherein two compounds may be usedsimultaneously in each of the multi-layers. The electron blocking layermay be placed between the hole transport layer (or the hole injectionlayer) and the light-emitting layer, and can confine the excitons withinthe light-emitting layer by blocking the overflow of electrons from thelight-emitting layer to prevent a light-emitting leakage.

In addition, the hole transport zone may comprise a p-doped holeinjection layer, a hole transport layer, and a light-emitting auxiliarylayer. Herein, the p-doped hole injection layer means a hole injectionlayer doped with a p-dopant. The p-dopant is a material capable ofimparting p-type semiconductor properties. The p-type semiconductorproperties mean the properties of injecting or transporting holes at theHOMO (highest occupied molecular orbital) energy level, i.e., theproperties of a material having a high hole conductivity.

The organic electroluminescent material of the present disclosure, e.g.,at least one of a hole injection material, a hole transport material, ahole auxiliary material, a light-emitting auxiliary material, anelectron blocking material, a light-emitting material, an electronbuffer material, a hole blocking material, an electron transportmaterial, an electron injection material and a light-emitting material(host material) may comprise a compound represented by formula 1. Theorganic electroluminescent material may be a hole transport materialand/or a light-emitting material. The organic electroluminescentmaterial may consist of the compound represented by formula 1 alone, ormay further comprise conventional materials included in the organicelectroluminescent material. For example, the organic electroluminescentmaterial of the present disclosure may further comprise at least onecompound represented by any one of formulas 11 to 15. When two or morematerials are comprised in one layer, they may be mixture-evaporated toform a layer, or may be separately co-evaporated at the same time toform a layer.

The organic electroluminescent device of the present disclosure maycomprise a first electrode, a second electrode, and at least one organiclayer between the first and second electrodes. One of the first andsecond electrodes may be an anode, and the other may be a cathode. Theorganic layer may comprise at least one light-emitting layer, and mayfurther comprise at least one layer selected from the group consistingof a hole injection layer, a hole transport layer, a hole auxiliarylayer, a light-emitting auxiliary layer, an electron transport layer, anelectron buffer layer, an electron injection layer, an interlayer, ahole blocking layer, and an electron blocking layer.

The first electrode and the second electrode may each be formed with atransmissive conductive material, a transflective conductive material,or a reflective conductive material. The organic electroluminescentdevice may be a top emission type, a bottom emission type, or both-sidesemission type depending on the type of the material forming the firstelectrode and the second electrode. In addition, the hole injectionlayer may be further doped with a p-dopant, and the electron injectionlayer may be further doped with an n-dopant.

The organic electroluminescent device of the present disclosure maycomprise the compound represented by formula 1, and may further compriseconventional materials included in the organic electroluminescentmaterial. The organic electroluminescent device comprising the organicelectroluminescent compound represented by formula 1 of the presentdisclosure may exhibit low driving voltage and/or high power efficiency.

In addition, the organic electroluminescent material according to oneembodiment of the present disclosure may be used as a light-emittingmaterial for a white organic light-emitting device. The white organiclight-emitting device has been suggested to have various structures suchas a side-by-side structure or a stacking structure depending on thearrangement of R (red), G (green) or YG (yellow green), and B (blue)light-emitting parts, or color conversion material (CCM) method, etc.The present disclosure may also be applied to such a white organiclight-emitting device. The organic electroluminescent material accordingto one embodiment of the present disclosure may also be used in anorganic electroluminescent device comprising a quantum dot (QD).

Furthermore, the present disclosure may provide a display system usingthe compound represented by formula 1. In other words, it is possible toproduce a display system or a lighting system by using the compound ofthe present disclosure. Specifically, it is possible to produce adisplay system, e.g., a display system for smart phones, tablets,notebooks, PCs, TVs, or cars; or a lighting system, e.g., an outdoor orindoor lighting system, by using the compound of the present disclosure.

Hereinafter, the preparation method of the compounds according to thepresent disclosure, the properties thereof, and the properties of theOLED comprising the organic electroluminescent compound according to thepresent disclosure will be explained in detail with reference to therepresentative compounds of the present disclosure. The followingexamples only describe the properties of the compound and the OLEDcomprising the same according to the present disclosure, but the presentdisclosure is not limited to the following examples.

Example 1: Preparation of Compound C-6

Synthesis of Compound 1-1

In a flask, 2-chloro-9,9-dimethyl-9H-fluorene (40.0 g, 150.0 mmol),(4-chloro-2-formylphenyl)boronic acid (55.3 g, 300.0 mmol),tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄) (12.1 g, 10.50mmol), and KOH (18.5 g, 330 mmol) were dissolved in 410 mL of o-xylene,82 mL of acetonitrile, and 164 mL of distilled water, and the mixturewas refluxed at 160° C. for 16 hours. After completion of the reaction,an organic layer was extracted with ethyl acetate. The residual moisturewas removed with magnesium sulfate. The residue was dried and separatedby column chromatography to obtain compound 1-1 (18.9 g, yield: 56.8%).

Synthesis of Compound 1-2

(Methoxymethyl)triphenylphosphonium chloride (25.9 g, 75.5 mmol) andcompound 1-1 (18.9 g, 56.8 mmol) were dissolved in 280 mL oftetrahydrofuran (THF). Thereafter, potassium tert-butoxide (tBuOK) (26.7g, 237.6 mmol) was added at 0° C., and the temperature was raised, andthen the mixture was stirred at room temperature for 3 hours. Aftercompletion of the reaction, an organic layer was extracted with ethylacetate. The residual moisture was removed with magnesium sulfate. Theresidue was dried and separated by column chromatography to obtaincompound 1-2 (20.3 g, yield: 99.0%).

Synthesis of Compound 1-3

Compound 1-2 (20.3 g, 56.3 mmol) was dissolved in 284 mL ofdichloromethane (DCM). Thereafter, boron trifluoride etherate (21.4 mL,170.4 mmol) was added at 0° C., the temperature was raised, and themixture was stirred at room temperature for 12 hours. After completionof the reaction, an aqueous NaHCO₃ solution was added, and an organiclayer was extracted with dichloromethane. The residual moisture wasremoved with magnesium sulfate. The residue was distilled under reducedpressure and separated by column chromatography to obtain compound 1-3(18.2 g, yield: 98.3%).

Synthesis of Compound C-6

Compound 1-3 (4.93 g, 15.0 mmol), bis(4-biphenylyl)amine (4.82 g, 15.0mmol), tris(dibenzylideneacetone)dipalladium(0) (687 mg, 0.75 mmol),tributylphosphine (0.728 mL, 1.50 mmol), and sodium tert-butoxide(NaOtBu) (4.32 g, 45.0 mmol) were dissolved in 75 mL of toluene, and themixture was refluxed at 145° C. for 3 hours. After completion of thereaction, the mixture was distilled under reduced pressure and separatedby column chromatography to obtain compound C-6 (4.7 g, yield: 54.7%).

MW M.P. (° C.) C-6 613.80 275.3

Example 2: Preparation of Compound C-7

Compound 1-3 (4.93 g, 15.0 mmol),N-([1,1′-biphenyl]4-yl)-9,9-dimethyl-9H-fluoren-2-amine (5.42 g, 15.0mmol), tris(dibenzylideneacetone)dipalladium(0) (687 mg, 0.75 mmol),tributylphosphine (0.728 mL, 1.50 mmol), and NaOtBu (4.32 g, 45.0 mmol)were dissolved in 75 mL of toluene, and the mixture was refluxed at 145°C. for 3 hours. After completion of the reaction, the mixture wasdistilled under reduced pressure and separated by column chromatographyto obtain compound C-7 (7.1 g, yield: 72.4%).

MW M.P. (° C.) C-7 653.87 173.2

Example 3: Preparation of Compound C-39

Synthesis of Compound 2-1

In a flask, 2-chloro-9,9-dimethyl-9H-fluorene (40.0 g, 150.0 mmol),(5-chloro-2-formylphenyl)boronic acid (55.3 g, 300.0 mmol), Pd(PPh₃)₄(12.1 g, 10.50 mmol), and KOH (18.5 g, 330 mmol) were dissolved in 410mL of o-xylene, 82 mL of acetonitrile, and 164 mL of distilled water,and the mixture was refluxed at 160° C. for 16 hours. After completionof the reaction, an organic layer was extracted with ethyl acetate. Theresidual moisture was removed with magnesium sulfate. The residue wasdried and separated by column chromatography to obtain compound 2-1(44.3 g, yield: 88.7%).

Synthesis of Compound 2-2

(Methoxymethyl)triphenylphosphonium chloride (60.1 g, 175.4 mmol) andcompound 2-1 (43.9 g, 132.0 mmol) were dissolved in 528 mL of THF.Thereafter, potassium tert-butoxide (tBuOK) (26.7 g, 237.6 mmol) wasadded at 0° C., and the temperature was raised, and then the mixture wasstirred at room temperature for 3 hours. After completion of thereaction, an organic layer was extracted with ethyl acetate. Theresidual moisture was removed with magnesium sulfate. The residue wasdried and separated by column chromatography to obtain compound 2-2(39.5 g, yield: 82.9%).

Synthesis of Compound 2-3

Compound 2-2 (39.5 g, 109.5 mmol) was dissolved in 545 mL of DCM.Thereafter, boron trifluoride etherate (41.3 mL, 328.5 mmol) was addedat 0° C., the temperature was raised, and the mixture was stirred atroom temperature for 12 hours. After completion of the reaction, anaqueous NaHCO₃ solution was added, and an organic layer was extractedwith dichloromethane. The residual moisture was removed with magnesiumsulfate. The residue was distilled under reduced pressure and solidifiedwith hexane to obtain compound 2-3 (30.4 g, yield: 84.4%).

Synthesis of Compound C-39

Compound 2-3 (4.34 g, 13.2 mmol),N-([1,1′-biphenyl]4-yl)-[1,1′:2′,1″-terphenyl]-2-amine (5.00 g, 12.6mmol), tris(dibenzylideneacetone)dipalladium(0) (691 mg, 0.755 mmol),tributylphosphine (0.733 mL, 1.51 mmol), and NaOtBu (3.63 g, 37.7 mmol)were dissolved in 63 mL of toluene, and the mixture was refluxed at 145°C. for 16 hours. After completion of the reaction, the mixture wasdistilled under reduced pressure and separated by column chromatographyto obtain compound C-39 (4.9 g, yield: 56.5%).

MW M.P. (° C.) C-39 689.90 289.3

Example 4: Preparation of Compound C-40

Compound 2-3 (4.34 g, 13.2 mmol),N-([1,1′:3′,1″-terphenyl]-4′-yl)dibenzo[b,d]furan-2-amine (5.18 g, 12.6mmol), tris(dibenzylideneacetone)dipalladium(0) (691 mg, 0.755 mmol),tributylphosphine (0.733 mL, 1.51 mmol), and NaOtBu (3.63 g, 37.7 mmol)were dissolved in 63 mL of toluene, and the mixture was refluxed at 145°C. for 3 hours. After completion of the reaction, the mixture wasdistilled under reduced pressure and separated by column chromatographyto obtain compound C-40 (6.4 g, yield: 72.3%).

MW M.P. (° C.) C-40 703.88 171.7

Example 5: Preparation of Compound C-26

Compound 2-3 (4.6 g, 14.0 mmol), bis(4-biphenylyl)amine (4.5 g, 14.0mmol), tris(dibenzylideneacetone)dipalladium(0) (641 mg, 0.7 mmol),tributylphosphine (0.680 mL, 1.40 mmol), and NaOtBu (4.04 g, 42.0 mmol)were dissolved in 75 mL of toluene, and the mixture was refluxed at 145°C. for 4 hours. After completion of the reaction, the mixture wasdistilled under reduced pressure and separated by column chromatographyto obtain compound C-26 (4.2 g, yield: 48.9%).

MW M.P. (° C.) C-26 613.80 221.2

Example 6: Preparation of Compound C-178

Compound 1-3 (5.06 g, 15.4 mmol),N-(3-(2-phenylpropan-2-yl)-phenyl)-[1,1′-biphenyl]-4-amine (5.09 g, 14.0mmol), tris(dibenzylideneacetone)dipalladium(0) (641 mg, 0.70 mmol),tributylphosphine (0.680 mL, 1.40 mmol), and NaOtBu (4.04 g, 42.0 mmol)were dissolved in 70 mL of toluene, and the mixture was refluxed at 145°C. for 3 hours. After completion of the reaction, the mixture wasdistilled under reduced pressure and separated by column chromatographyto obtain compound C-178 (7.3 g, yield: 79.5%).

MW M.P. (° C.) C-178 655.88 273.8

Example 7: Preparation of Compound C-179

Compound 2-3 (5.06 g, 15.4 mmol),9,9-diphenyl-N-phenyl-9H-fluoren-2-amine (5.73 g, 14.0 mmol),tris(dibenzylideneacetone)dipalladium(0) (641 mg, 0.700 mmol),tributylphosphine (0.680 mL, 1.40 mmol), and NaOtBu (4.04 g, 42.0 mmol)were dissolved in 70 mL of toluene, and the mixture was refluxed at 145°C. for 4 hours. After completion of the reaction, the mixture wasdistilled under reduced pressure and separated by column chromatographyto obtain compound C-179 (8.0 g, yield: 81.4%).

MW M.P. (° C.) C-179 701.91 243.0

Example 8: Preparation of Compound C-180

Compound 2-3 (6.04 g, 18.4 mmol), N-phenyldibenzo[b,d]selenophen-4-amine(5.64 g, 17.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (801 mg,0.875 mmol), tributylphosphine (0.850 mL, 1.75 mmol), and NaOtBu (5.05g, 52.5 mmol) were dissolved in 88 mL of toluene, and the mixture wasrefluxed at 145° C. for 2 hours. After completion of the reaction, themixture was distilled under reduced pressure and separated by columnchromatography to obtain compound C-180 (9.0 g, yield: 83.6%).

MW M.P. (° C.) C-180 614.65 170.7

Example 9: Preparation of Compound C-183

In a flask, compound 1-4 (0.25 g, 0.5 mmol),2-bromo-N-(4-(naphthalen-2-yl)phenyl)-N-phenyl aniline (0.23 g, 0.55mmol), PdCl₂(Amphos) (0.017 g, 0.025 mmol), Na₂CO₃ (0.1 g, 1.0 mmol),Aliquot 336 (0.01 g, 0.025 mmol), 5 mL of toluene, 1 mL of H₂O wereadded, and the mixture was stirred at 120° C. for 18 hours. Aftercompletion of the reaction, the mixture was cooled to room temperature,and distilled under reduced pressure, and then separated by columnchromatography to obtain compound C-183 (0.1 g, yield: 29%).

MW C-183 663.86

Example 10: Preparation of Compound C-185

Synthesis of Compound 1

In a flask, 2-bromo-9,9-diphenyl-9H-fluorene (30 g, 75.5 mmol),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (28 g, 113.2mmol), KOAc (14.8 g, 151 mmol), and PdCl₂(PPh₃)₂ (4.3 g, 3.77 mmol) weredissolved in 500 mL of 1,4-dioxane, and the mixture was stirred underreflux at 150° C. for 3 hours. After completion of the reaction, anorganic layer was extracted with ethyl acetate and the residual moisturewas removed with magnesium sulfate. The residue was dried and separatedby column chromatography to obtain compound 1 (35 g, yield: 100%).

Synthesis of Compound 2

In a flask, compound 1 (35 g, 78.7 mmol), 2-bromo-6-chlorobenzaldehyde(17 g, 78.7 mmol), Pd(PPh₃)₄ (4.5 g, 3.93 mmol), K₂CO₃ (21 g, 154.8mmol), 546 mL of toluene, 273 mL of EtOH, and 273 mL of H₂O were added,and the mixture was stirred under reflux at 130° C. for 3 hours. Aftercompletion of the reaction, methanol and water were added and stirred,and the solvent was removed by filtration under reduced pressure. Afterseparation by column chromatography, methanol was added to produce asolid. The resulting solid was filtered under reduced pressure to obtaincompound 2 (30 g, yield: 83.4%).

Synthesis of Compound 3

In a flask, compound 2 (30 g, 65.6 mmol),(methoxymethyl)triphenylphosphonium chloride (33 g, 98.5 mmol), andKOtBu (15.1 g, 98.5 mmol) were dissolved in 326 mL of THF, and themixture was stirred at room temperature for 2 hours. After completion ofthe reaction, MeOH and water were added and stirred, and the solvent wasremoved by filtration under reduced pressure. After separation by columnchromatography, MeOH was added to produce a solid. The resulting solidwas filtered under reduced pressure to obtain compound 3 (40 g, yield:over yield %).

Synthesis of Compound 4

In a flask, compound 3 (40 g, 82.4 mmol) was dissolved in 500 mL ofmethylene chloride, and TfOH (trifluoromethane sulfonic acid) (7.2 mL,82.4 mmol) was slowly added dropwise, followed by stirring at roomtemperature for 1 hour. After completion of the reaction, MeOH and waterwere added and stirred, and the solvent was removed by filtration underreduced pressure. After separation by column chromatography, MeOH wasadded to produce a solid. The resulting solid was filtered under reducedpressure to obtain compound 4 (24 g, yield: 64%).

Synthesis of Compound C-185

In a flask, compound 4 (5 g, 15.21 mmol), compound 5 (5.4 g, 16.73mmol), NaOtBu (2.9 g, 30.42 mmol), S-Phos (499 mg, 1.21 mmol), andPd₂(dba)₃ (696 mg, 0.76 mmol) were dissolved in 76 mL of xylene, and themixture was stirred under reflux at 130° C. for 12 hours. Aftercompletion of the reaction, an organic layer was extracted with ethylacetate. The residual moisture was removed with magnesium sulfate. Theresidue was dried and separated by column chromatography to obtaincompound C-185 (3.5 g, yield: 37.1%).

MW M.P. (° C.) C-185 751.93 309

Device Examples 1 to 7: Producing a Red OLED Comprising the OrganicElectroluminescent Compound According to the Present Disclosure

OLEDs according to the present disclosure were produced. A transparentelectrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glasssubstrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to anultrasonic washing with acetone and isopropyl alcohol, sequentially, andthen was stored in isopropyl alcohol. The ITO substrate was then mountedon a substrate holder of a vacuum vapor deposition apparatus. CompoundHI-1 as a hole injection compound was introduced into a cell of thevacuum vapor deposition apparatus, and compound HT-1 as a hole transportcompound was introduced into another cell of the vacuum vapor depositionapparatus. The two materials were evaporated at different rates, andcompound HI-1 was deposited in a doping amount of 3 wt % based on thetotal amount of compound HI-1 and compound HT-1 to form a hole injectionlayer having a thickness of 10 nm on the ITO substrate. Next, compoundHT-1 was deposited on the hole injection layer to form a first holetransport layer having a thickness of 90 nm. The compound of the secondhole transport layer shown in Table 1 below was then introduced intoanother cell of the vacuum vapor deposition apparatus and was evaporatedby applying an electric current to the cell, thereby forming a secondhole transport layer having a thickness of 60 nm on the first holetransport layer. After forming the hole injection layer and the holetransport layers, a light-emitting layer was formed thereon as follows:Compound RH-1 and compound RH-2 were introduced into two cells of thevacuum vapor deposition apparatus as hosts, and compound D-39 wasintroduced into another cell as a dopant. Compound RH-1 and compoundRH-2 as hosts were evaporated at a rate of 5:5 and the dopant materialwas simultaneously evaporated at a different rate, and the dopant wasdeposited in a doping amount of 2 wt % based on the total amount of thehosts and the dopant to form a light-emitting layer having a thicknessof 40 nm on the second hole transport layer. Next, compound HBL wasdeposited as an electron buffer layer having a thickness of 5 nm on thelight-emitting layer. Thereafter, compound ETL-1 and compound EIL-1 wereevaporated in a weight ratio of 5:5 to deposit an electron transportlayer having a thickness of 30 nm on the electron buffer layer. Afterdepositing compound EIL-1 as an electron injection layer having athickness of 2 nm on the electron transport layer, an Al cathode havinga thickness of 80 nm was deposited on the electron injection layer byanother vacuum vapor deposition apparatus. Thus, an OLED was produced.All the materials used for producing the OLED were purified by vacuumsublimation at 10⁻⁶ torr.

Comparative Example 1: Producing a Red OLED Comprising a ComparativeCompound

An OLED was produced in the same manner as in Device Example 1, exceptthat compound A was used as the second hole transport layer.

The driving voltage, power efficiency, and CIEx,y (1931) chromaticitycoordinates at a luminance of 1,000 nit of the OLEDs produced in DeviceExamples 1 to 7, and Comparative Example 1 are provided in Table 1below.

TABLE 1 Second Hole Driving Power CIE Chromaticity Transport VoltageEfficiency Coordinates Layer [V] [lm/W] (x, y) Device C-6 2.8 33.1(0.661, 0.339) Example 1 Device C-7 2.8 30.1 (0.657, 0.342) Example 2Device C-39 2.9 28.1 (0.656, 0.343) Example 3 Device C-40 2.8 33.0(0.658, 0.341) Example 4 Device C-178 3.0 26.8 (0.656, 0.343) Example 5Device C-180 3.0 26.0 (0.654, 0.344) Example 6 Device C-179 2.8 34.5(0.656, 0.343) Example 7 Comparative A 4.2 21.4 (0.662, 0.338) Example 1

From Table 1 above, it can be confirmed that the organicelectroluminescent device comprising the compound according to thepresent disclosure as a hole transport layer material exhibits superiorproperties, particularly lower driving voltage and/or higher powerefficiency compared to the organic electroluminescent device using theconventional compound.

Without being limited by theory, it is understood that the excellenteffect of the compound of the present disclosure as described above isdue to the following properties. The indeno[1,2-b]phenanthrene compoundof the present disclosure may exhibit sufficient triplet energy in thehole transport layer due to the high triplet energy of phenanthrene. Inaddition, indeno[1,2-b]phenanthrene core does not contain a heteroatom,which has additional lone pairs that can possibly interrupt holetransition, thereby allowing the hole flow to be properly regulated.Thus, the performance of the device including the same can be improved.Furthermore, indeno[1,2-b]phenanthrene may show a high glass transitiontemperature (Tg) and/or a high refractive index, which is advantageousin terms of morphological stability, since heat generation cannot beavoided during OLED device operation.

Device Examples 8 to 10: Producing a Red OLED Comprising the OrganicElectroluminescent Compound According to the Present Disclosure

OLEDs according to the present disclosure were produced. A transparentelectrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glasssubstrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to anultrasonic washing with acetone and isopropyl alcohol, sequentially, andthen was stored in isopropyl alcohol. The ITO substrate was then mountedon a substrate holder of a vacuum vapor deposition apparatus. CompoundHI-1 was introduced into a cell of the vacuum vapor depositionapparatus, and compound HT-2 was introduced into another cell of thevacuum vapor deposition apparatus. The two materials were evaporated atdifferent rates, and compound HI-1 was deposited in a doping amount of 3wt % based on the total amount of compound HI-1 and compound HT-2 toform a hole injection layer having a thickness of 10 nm on the ITOsubstrate. Next, compound HT-2 was deposited on the hole injection layerto form a first hole transport layer having a thickness of 80 nm.Compound HT-3 was then introduced into another cell of the vacuum vapordeposition apparatus and was evaporated by applying an electric currentto the cell, thereby forming a second hole transport layer having athickness of 60 nm on the first hole transport layer. After forming thehole injection layer and the hole transport layers, a light-emittinglayer was formed thereon as follows: the first and second host compoundsshown in Table 2 below were introduced into two cells of the vacuumvapor deposition apparatus as hosts, and compound D-39 was introducedinto another cell as a dopant. The two host materials were evaporated ata rate of 1:1 and the dopant material was simultaneously evaporated at adifferent rate, and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the hosts and the dopant to form alight-emitting layer having a thickness of 40 nm on the second holetransport layer. Thereafter, compound ETL-2 and compound EIL-1 wereevaporated in a weight ratio of 50:50 to deposit an electron transportlayer having a thickness of 35 nm on the light-emitting layer. Afterdepositing compound EIL-1 as an electron injection layer having athickness of 2 nm on the electron transport layer, an Al cathode havinga thickness of 80 nm was deposited on the electron injection layer byanother vacuum vapor deposition apparatus. Thus, an OLED was produced.All the materials used for producing the OLED were purified by vacuumsublimation at 10⁻⁶ torr.

Comparative Example 2: Producing an OLED Comprising a ComparativeCompound as a Single Host

An OLED was produced in the same manner as in Device Example 8, exceptthat compound RH-2 was used as a single host of the light-emittinglayer.

Comparative Example 3: Producing an OLED Comprising a ComparativeCompound as the First Host

An OLED was produced in the same manner as in Device Example 8, exceptthat the first host compound shown in Table 2 below was used as thefirst host of the light-emitting layer.

The driving voltage, luminous efficiency, and light-emitting color at aluminance of 1,000 nit, and the time taken for luminance to decreasefrom 100% to 95% (lifetime; T95) at a luminance of 10,000 nit of theOLEDs produced in Device Examples 8 to 10, and Comparative Examples 2and 3 are provided in Table 2 below.

TABLE 2 Driving Luminous Light- Lifetime First Second Voltage EfficiencyEmitting (T95) Host Host [V] [cd/A] Color [hr] Device C-26 RH-2 3.0 35.1Red 120 Example 8 Device C-6 RH-2 3.0 33.0 Red 293 Example 9 DeviceC-179 RH-2 3.0 34.6 Red 142 Example 10 Comparative — RH-2 3.5 31.8 Red18 Example 2 Comparative A RH-2 3.4 33.1 Red 113 Example 3

From Table 2 above, it can be confirmed that the organicelectroluminescent device comprising the compound according to thepresent disclosure as a host material exhibits superior properties,particularly low driving voltage, high luminous efficiency, and/or longlifetime properties compared to the organic electroluminescent deviceusing the conventional compound.

The compounds used in the Device Examples and the Comparative Examplesare shown in Table 3 below.

TABLE 3 Hole Injection Layer/ Hole Transport Layer

Second Hole Transport Layer

Light-Emitting Layer

Electron Buffer Layer

Electron Transport Layer/Electron Injection Layer

1. An organic electroluminescent compound represented by the following formula 1:

in formula 1, R′₁ and R′₂, each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R′₁ and R′₂ may be linked to each other to form a ring(s), in which R′₁ and R′₂ may be the same as or different from each other; R₁ to R₄, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), or -L₁-N—(Ar₁)(Ar₂); or may be linked to an adjacent substituent to form a ring(s); with the proviso that any one of R₁'s to R₄'s represents -L₁-N—(Ar₁)(Ar₂); L₁ represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar₁ and Ar₂, each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and m and p, each independently, represent an integer of 4; n and o, each independently, represent an integer of 2; and each of R₁ to each of R₄ may be the same or different.
 2. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by the following formula 1-1:

in formula 1-1, R′₁, R′₂, R₁ to R₄, and m to p are as defined in claim
 1. 3. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 1-1-1 to 1-1-4:

in formulas 1-1-1 to 1-1-4, R′₁, R′₂, L₁, Ar₁, Ar₂, and m to p are as defined in claim 1; m′ and p′, each independently, represent an integer of 3; n′ and o′, each independently, represent an integer of 1; and R₁ to R₄, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s); or may be linked to an adjacent substituent to form a ring(s).
 4. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 1-1-1-1 to 1-1-1-12:

in formulas 1-1-1-1 to 1-1-1-12, R′₁, R′₂, L₁, Ar₁, Ar₂, and m to p are as defined in claim 1; m′ and p′, each independently, represent an integer of 3; n′ and o′, each independently, represent an integer of 1; and R₁ to R₄, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, or a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s); or may be linked to an adjacent substituent to form a ring(s).
 5. The organic electroluminescent compound according to claim 1, wherein the substituent(s) of the substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring group of an aliphatic ring(s) and an aromatic ring(s), each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a phosphineoxide; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl unsubstituted or substituted with a (C6-C30)aryl(s); a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s) and (3- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; a fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s); a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a (C6-C30)arylphosphinyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.
 6. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of the following:


7. An organic electroluminescent material comprising the organic electroluminescent compound according to claim
 1. 8. The organic electroluminescent material according to claim 7, further comprising at least one compound represented by any one of the following formulas 11 to 15:

in formulas 11 to 15, Ma represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; La represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; A represents S, O, N(Re), C(Rf)(Rg), Te, or Se; ring B represents a naphthalene ring or a phenanthrene ring; Ra to Rd, and Rh to Rk, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or may be linked to an adjacent substituent to form a ring(s); Re to Rg, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; and Rf and Rg may be linked to each other to form a ring(s); w to y, q, and r, each independently, represent an integer of 1 to 4; z represents an integer of 1 to 3; and a and t, each independently, represent an integer of 1 or 2; n represents an integer of 1 to 9; and each of Ra to each of Rd, each of Ri to each of Rk, and each of La may be the same or different; and the heteroaryl(ene) comprises at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Te, and Se.
 9. The organic electroluminescent material according to claim 8, wherein the compound represented by formula 11 is selected from the group consisting of the following:


10. The organic electroluminescent material according to claim 8, wherein the compound represented by formula 12 is selected from the group consisting of the following:


11. The organic electroluminescent material according to claim 8, wherein the compound represented by formula 13 or 14 is selected from the group consisting of the following:


12. The organic electroluminescent material according to claim 8, wherein the compound represented by formula 15 is selected from the group consisting of the following:


13. An organic electroluminescent device comprising the organic electroluminescent compound according to claim
 1. 